Evidence for the formation of acylboronate intermediates in the carbonylation reactions of organoboranes

Journal Article · Thu Dec 01 04:00:00 EST 1994 · Organometallics; (United States)

DOI:https://doi.org/10.1021/om00024a069· OSTI ID:6736429

Kabalka, G W; Gotsick, J T; Pace, R D; Li, N S ^[1]

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1. Univ. of Tennessee, Knoxville, TN (United States)

Trialkylboranes react with acyllithium reagents to yield ketones after oxidation with hydrogen peroxide. The ketones contain one alkyl group supplied by the alkyllithium reagent and one alkyl group supplied by the organoborane. The experimental results support the hypothesis that an acylboronate is an intermediate in the reactions of organoboranes with carbon monoxide. The yields are modest due to an apparent competition between carbon monoxide and organoborane for the alkyllithium needed to generate the acyl anion. 13 refs., 2 tabs.

• OSTI ID: 6736429
• Journal Information: Organometallics; (United States), Journal Name: Organometallics; (United States) Vol. 13:12; ISSN ORGND7; ISSN 0276-7333
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400102 -- Chemical & Spectral Procedures
400201* -- Chemical & Physicochemical Properties
ALKALI METAL COMPOUNDS
BORANES
BORON COMPOUNDS
CARBON COMPOUNDS
CARBON MONOXIDE
CARBON OXIDES
CARBONYLATION
CHALCOGENIDES
CHEMICAL REACTIONS
CHROMATOGRAPHY
COMPILED DATA
DATA
GAS CHROMATOGRAPHY
HYDRIDES
HYDROGEN COMPOUNDS
HYDROGEN PEROXIDE
INFORMATION
KETONES
LITHIUM COMPOUNDS
MASS SPECTROSCOPY
NUMERICAL DATA
ORGANIC COMPOUNDS
ORGANOMETALLIC COMPOUNDS
OXIDATION
OXIDES
OXYGEN COMPOUNDS
PEROXIDES
REACTION INTERMEDIATES
SEPARATION PROCESSES
SPECTROSCOPY